NP-MRD: Showing NP-Card for 8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one (NP0287542)

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Record Information

Version

2.0

Created at

2022-09-09 16:43:54 UTC

Updated at

2022-09-09 16:43:55 UTC

NP-MRD ID

NP0287542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

Description

Synerazol belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one is found in Aspergillus fumigatus. 8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one was first documented in 2004 (PMID: 15712670). Based on a literature review a small amount of articles have been published on Synerazol (PMID: 35323689) (PMID: 19179074) (PMID: 19168986) (PMID: 15989349).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092218432D          

 30 33  0  0  0  0            999 V2000
   -2.1654   -3.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -2.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168   -2.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4879   -0.5712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3596    0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1083   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -0.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4514   -2.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668   -1.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 18 29  1  0  0  0  0
 13 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    7.7522   -1.8699   -0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6835   -0.6362   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3675    0.0301   -1.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3598   -0.3903   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0320    0.3116   -0.3695 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2180   -0.1358   -1.4747 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364   -0.4609   -0.1704 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5557    0.0480    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    1.2322    0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    2.4347    0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    1.2321    1.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312    1.9916    2.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128    0.0738    0.4932 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.2420    0.4721   -0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915    1.4003   -1.6672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483   -0.1844   -1.0975 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6648   -1.0727   -0.0292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1496   -2.3561   -0.2779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -2.9334   -1.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1003   -1.1059    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -2.2702    0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0149    0.0066    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606   -0.2240    0.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2957    0.7777    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9407    2.0733    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6545    2.3450    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064    1.3243    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9038   -0.5141    1.2055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6425    0.3606    1.9397 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1670   -2.6637   -0.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4201   -1.6551    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8378   -2.1417   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4322    0.0864   -0.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9417   -0.8813   -2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250    0.9269   -1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692   -1.2759    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247    1.3853   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0175   -1.5766    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974    3.2205    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3893    2.9405    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353    2.2206    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    1.9438   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -3.9395   -1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -2.2795   -2.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7368   -3.0822   -1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6414   -1.2426    0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3287    0.5059    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7145    2.8327    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3823    3.3800   -0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    1.5953   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5568   -1.4007    1.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974   -0.0899    2.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  6
 13 29  1  0
 29 30  1  0
 29 18  1  0
 18 19  1  6
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 18 17  1  0
 17 15  2  0
 15 16  1  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  7  5  1  0
 14  8  1  0
 28 23  1  0
 15 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  1
  7 39  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
 29 52  1  1
 30 53  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 16 43  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 28 51  1  0
M  END


  Mrv1652309092218432D          

 30 33  0  0  0  0            999 V2000
   -2.1654   -3.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -2.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168   -2.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4879   -0.5712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3596    0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -1.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1083   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8930   -0.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4514   -2.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6668   -1.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
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 26 27  1  0  0  0  0
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 23 28  1  0  0  0  0
 18 29  1  0  0  0  0
 13 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287542

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C\C1OC1C1=C(C)C(=O)C2(O1)C(O)C(OC)(N=C2O)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H23NO7/c1-4-5-11-14-16(29-14)15-12(2)17(24)21(30-15)19(26)22(28-3,23-20(21)27)18(25)13-9-7-6-8-10-13/h5-11,14,16,19,26H,4H2,1-3H3,(H,23,27)/b11-5+

> <INCHI_KEY>
UCUHTBUWKCQZNJ-VZUCSPMQSA-N

> <FORMULA>
C22H23NO7

> <MOLECULAR_WEIGHT>
413.426

> <EXACT_MASS>
413.147452085

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.06035743208321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-benzoyl-2-{3-[(1E)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

> <JCHEM_LOGP>
3.215449819999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200196160475011

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.45551829577514

> <JCHEM_PKA_STRONGEST_BASIC>
-3.924385814612775

> <JCHEM_POLAR_SURFACE_AREA>
117.95

> <JCHEM_REFRACTIVITY>
107.4115

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-benzoyl-2-{3-[(1E)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.042  -7.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.796  -6.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.957  -4.749   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.711  -3.844   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.872  -2.312   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.777  -1.066   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.941   3.481   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.275   2.016   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.799   3.481   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       4.740   1.540   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.740  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.271   0.161   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.898   1.568   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.060  -1.506   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.915  -2.537   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.524  -1.982   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.669  -0.952   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.134  -1.428   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.454  -2.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.309  -3.964   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.845  -3.489   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.799  -1.941   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    7                                                       
CONECT    7    6    5    8                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   29                                             
CONECT   14   13    8                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   21   29                                             
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   18   13   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₃NO₇

Average Mass

413.4260 Da

Monoisotopic Mass

413.14745 Da

IUPAC Name

8-benzoyl-2-{3-[(1E)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

Traditional Name

8-benzoyl-2-{3-[(1E)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one

CAS Registry Number

Not Available

SMILES

CC\C=C\C1OC1C1=C(C)C(=O)C2(O1)C(O)C(OC)(N=C2O)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C22H23NO7/c1-4-5-11-14-16(29-14)15-12(2)17(24)21(30-15)19(26)22(28-3,23-20(21)27)18(25)13-9-7-6-8-10-13/h5-11,14,16,19,26H,4H2,1-3H3,(H,23,27)/b11-5+

InChI Key

UCUHTBUWKCQZNJ-VZUCSPMQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus fumigatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Benzoyl
Aryl alkyl ketone
Monocyclic benzene moiety
3-furanone
Pyrrolidone
2-pyrrolidone
Benzenoid
Dihydrofuran
Pyrrolidine
Vinylogous ester
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Alcohol
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.22	ChemAxon
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.41 m³·mol⁻¹	ChemAxon
Polarizability	43.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017082

Chemspider ID

4942993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438524

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Desouky SE, Abu-Elghait M, Fayed EA, Selim S, Yousuf B, Igarashi Y, Abdel-Wahab BA, Mohammed Alsuhaibani A, Sonomoto K, Nakayama J: Secondary Metabolites of Actinomycetales as Potent Quorum Sensing Inhibitors Targeting Gram-Positive Pathogens: In Vitro and In Silico Study. Metabolites. 2022 Mar 15;12(3). pii: metabo12030246. doi: 10.3390/metabo12030246. [PubMed:35323689 ]
Ishikawa M, Ninomiya T, Akabane H, Kushida N, Tsujiuchi G, Ohyama M, Gomi S, Shito K, Murata T: Pseurotin A and its analogues as inhibitors of immunoglobulin E [correction of immunoglobuline E] production. Bioorg Med Chem Lett. 2009 Mar 1;19(5):1457-60. doi: 10.1016/j.bmcl.2009.01.029. Epub 2009 Jan 15. [PubMed:19179074 ]
Ishikawa M, Ninomiya T: Chemical modification of pseurotin A: one-pot synthesis of synerazol and pseurotin E and determination of absolute stereochemistry of pseurotin E. J Antibiot (Tokyo). 2008 Nov;61(11):692-5. doi: 10.1038/ja.2008.99. [PubMed:19168986 ]
Hayashi Y, Shoji M, Mukaiyama T, Gotoh H, Yamaguchi S, Nakata M, Kakeya H, Osada H: First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry. J Org Chem. 2005 Jul 8;70(14):5643-54. doi: 10.1021/jo050664x. [PubMed:15989349 ]
Igarashi Y, Yabuta Y, Sekine A, Fujii K, Harada K, Oikawa T, Sato M, Furumai T, Oki T: Directed biosynthesis of fluorinated pseurotin A, synerazol and gliotoxin. J Antibiot (Tokyo). 2004 Nov;57(11):748-54. doi: 10.7164/antibiotics.57.748. [PubMed:15712670 ]
LOTUS database [Link]

Showing NP-Card for 8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one (NP0287542)

MOL for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D MOL for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D SDF for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D-SDF for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

PDB for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D PDB for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

SMILES for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

INCHI for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

Structure for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)

3D Structure for NP0287542 (8-benzoyl-2-{3-[(1e)-but-1-en-1-yl]oxiran-2-yl}-6,9-dihydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]nona-2,6-dien-4-one)